Acetaldehyde → HCID 20043106, compound

HRID 1762279Notes

Reaction equation

HRID 1762279 reaction equation
Cl.[CH:2](=[O:4])[CH3:3].[CH2:5]([CH:7]1[O:11][C:10](=[O:12])[NH:9][CH2:8]1)[CH3:6].C[O-].[Na+].[CH2:16](O)[CH3:17]>>[CH2:2]([O:4][CH:16]([N:9]1[CH2:8][CH:7]([CH2:5][CH3:6])[O:11][C:10]1=[O:12])[CH3:17])[CH3:3]

Participants

6

Reactant 5

HCID 177Acetaldehyde2×HCID 313Hydrochloric AcidHCID 702EthanolHCID 10942334Sodium MethoxideHCID 137045895-Ethyl-1,3-oxazolidin-2-one

Product 1

HCID 20043106HCID 20043106, compound

Procedure

In a three-necked flask equipped with a mechanical stirrer and reflux condenser, ethanol is acidified to a pH of 0.5-1.5 with 8 percent methanolic HCl. To the cooled alcohol is added acetaldehyde. The addition is so conducted that the temperature of the mixture stays under 40° C. The solution is stirred at room temperature for 2 hours after the completion of addition. The mole ratio of alcohol to acetaldehyde is about 1.5:1. 5-Ethyl-2-oxazolidinone (mole ratio of acetaldehyde to 2-oxazolidinone is 3:1) is added dropwise to the solution. The mixture is then stirred for 24 hours at 45° C. The mixture is then neutralized to a pH of 6.5-8 with a solution of sodium methoxide. After removing the unconsumed hemiacetal and alcohol under vacuum, the liquid 3-(1-ethoxyethyl)-5-ethyl-2-oxazolidinone is obtained.

Workup

  1. customIn a three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionThe addition
  4. customstays under 40° C
  5. additionafter the completion of addition
  6. stirringThe mixture is then stirred for 24 hours at 45° C
  7. customAfter removing the unconsumed hemiacetal and alcohol under vacuum

Sources & evidence

ORD record
ord-8fe8e86671644fe9b92ec6d93ca30103
Source dataset
uspto-grants-1989_05
Patent number
US04831153

Reaction notes

Loading…